US6005085A - Condensed azo compounds and process for preparing the same - Google Patents

Condensed azo compounds and process for preparing the same Download PDF

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US6005085A
US6005085A US09/194,500 US19450098A US6005085A US 6005085 A US6005085 A US 6005085A US 19450098 A US19450098 A US 19450098A US 6005085 A US6005085 A US 6005085A
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optionally branched
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Ryuzo Ueno
Masaya Kitayama
Kenji Minami
Hiroyuki Wakamori
Katsunori Tanikawa
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Ueno Seiyaku Oyo Kenkyujo KK
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
    • C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
    • C07C245/10—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/26—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/02—Disazo dyes
    • C09B33/147—Disazo dyes in which the coupling component is a bis -(-o-hydroxy-carboxylic- acid amide)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
    • C09B62/046—Specific dyes not provided for in group C09B62/06 - C09B62/10
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0675—Azo dyes
    • G03G5/0679—Disazo dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0675—Azo dyes
    • G03G5/0679—Disazo dyes
    • G03G5/0681—Disazo dyes containing hetero rings in the part of the molecule between the azo-groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile

Definitions

  • the present invention relates to novel condensed azo compounds and a process for preparing the same.
  • the present invention is characterized in that it provides azo coloring materials having excellent properties such as excellent water resistance, chemical resistance, solvent resistance, and heat resistance. Furthermore, the present invention aims to provide a series of azo compounds of which color and vividness can be regulated by appropriately selecting the substituents on the molecules.
  • the present invention provides novel condensed azo compounds using bisamide compounds prepared from 2-hydroxynaphthalene-3,6-dicarboxylic acid as couplers, as well as coloring materials comprising the same, and a process for preparing said condensed azo compounds.
  • the present invention relates to a condensed azo compound represented by the general formula [I], [II], or [III]: ##STR1## wherein, Y represents --(CONH) n --X or --COR; Y' represents --(CONH) n --X' or --COR';
  • X and X' each represent an optionally branched alkyl group of 1-16 carbon atoms, an optionally substituted aromatic group, or an optionally substituted heterocyclic group having conjugated double bonds;
  • n an integer 1 or 2;
  • R and R' each represent a hydroxyl group, an optionally branched alkoxy group of 1-30 carbon atoms, a benzyloxy group, a phenyloxy group, or a phenacyloxy group, provided that if one of R and R' is a hydroxyl group, then it may form an acceptable salt;
  • R 2 and R 2 ' each represent a hydrogen atom, an optionally branched alkyl group of 1-6 carbon atoms, an acyl group of 1-6 carbon atoms, or a phenylalkyl group;
  • Q and Q' each represent an optionally branched alkyl group of 1-6 carbon atoms, an optionally branched alkoxy group of 1-6 carbon atoms, a halogen atom, a nitro group, or a nitroso group;
  • n and m' each represent an integer from 0 to 3, provided that if m or m' is 1, then Q or Q' may bind to either of the two fused rings, and if m or m' is 2 or 3, then Q or Q' may bind to one or both of the fused rings or may form a ring together with the two fused rings;
  • A represents an optionally branched alkylene group of 2-12 carbon atoms or a cyclic group having conjugated double bonds
  • Z and Z' each represent an optionally substituted monovalent aromatic group
  • the azo compound of the present invention has non-condensed amide group(s), hydroxyl group(s), or alkoxy group(s), and in particular when the amide group is an aromatic amide group, color and vividness of the compound can be regulated by introducing an appropriate substituent(s) into such aromatic group.
  • coloring materials refers to, for example, dyes, pigments, inks, paints, printing inks, and organic photoconductive materials.
  • the present invention relates to a process for preparing a condensed azo compound represented by the general formula [I], [II], or [III]: ##STR2## wherein, Y represents --(CONH) n --X or --COR; Y' represents --(CONH) n --X' or --COR';
  • X and X' each represent an optionally branched alkyl group of 1-16 carbon atoms, an optionally substituted aromatic group, or an optionally substituted heterocyclic group having conjugated double bonds;
  • n an integer 1 or 2;
  • R and R' each represent a hydroxyl group, an optionally branched alkoxy group of 1-30 carbon atoms, a benzyloxy group, a phenyloxy group, or a phenacyloxy group, provided that if one of R and R' is a hydroxyl group, then it may form an acceptable salt;
  • R 2 and R 2 ' each represent a hydrogen atom, an optionally branched alkyl group of 1-6 carbon atoms, an acyl group of 1-6 carbon atoms, or a phenylalkyl group;
  • Q and Q' each represent an optionally branched alkyl group of 1-6 carbon atoms, an optionally branched alkoxy group of 1-6 carbon atoms, a halogen atom, a nitro group, or a nitroso group;
  • n and m' each represent an integer from 0 to 3, provided that if m or m' is 1, then Q or Q' may bind to either of the two fused rings, and if m or m' is 2 or 3, then Q or Q' may bind to one or both of the fused rings or may form a ring together with the two fused rings;
  • A represents an optionally branched alkylene group of 2-12 carbon atoms or a cyclic group having conjugated double bonds
  • Z and Z' each represent an optionally substituted monovalent aromatic group; the process being characterized in that an aromatic diazonium compound represented by the general formula [VII] or [VII']:
  • Z and Z' each represent an optionally substituted monovalent aromatic group
  • X and X' each represent an optionally branched alkyl group of 1-16 carbon atoms, an optionally substituted aromatic group, or an optionally substituted heterocyclic group having conjugated double bonds;
  • n an integer 1 or 2;
  • R and R' each represent a hydroxyl group, an optionally branched alkoxy group of 1-30 carbon atoms, a benzyloxy group, a phenyloxy group, or a phenacyloxy group, provided that if one of R and R' is a hydroxyl group, then it may form an acceptable salt;
  • R 2 and R 2 ' each represent a hydrogen atom, an optionally branched alkyl group of 1-6 carbon atoms, an acyl group of 1-6 carbon atoms, or a phenylalkyl group;
  • Q and Q' each represent an optionally branched alkyl group of 1-6 carbon atoms, an optionally branched alkoxy group of 1-6 carbon atoms, a halogen atom, a nitro group, or a nitroso group;
  • n and m' each represent an integer from 0 to 3, provided that if m or m' is 1, then Q or Q' may bind to either of the two fused rings, and if m or m' is 2 or 3, then Q or Q' may bind to one or both of the fused rings or may form a ring together with the two fused rings;
  • A represents an optionally branched alkylene group of 2-12 carbon atoms or a cyclic group having conjugated double bonds.
  • the present invention also relates to novel bis(aminocarbonylnaphthol) derivatives represented by the general formula [VIII'], [IX'], or [X']: ##STR4## wherein, Y represents --(CONH) n --X or --COR; Y' represents --(CONH) n --X' or --COR';
  • X and X' each represent an optionally branched alkyl group of 1-16 carbon atoms, an optionally substituted aromatic group, or an optionally substituted heterocyclic group having conjugated double bonds;
  • n an integer 1 or 2;
  • R and R' each represent a hydroxyl group, an optionally branched alkoxy group of 1-6 carbon atoms, a benzyloxy group, a phenyloxy group, or a phenacyloxy group, provided that if one of R and R' is a hydroxyl group, then it may form an acceptable salt;
  • R 2 and R 2 ' each represent a hydrogen atom, an optionally branched alkyl group of 1-6 carbon atoms, an acyl group of 1-6 carbon atoms, or a phenylalkyl group;
  • Q and Q' each represent an optionally branched alkyl group of 1-6 carbon atoms, an optionally branched alkoxy group of 1-6 carbon atoms, a halogen atom, a nitro group, or a nitroso group;
  • n and m' each represent an integer from 0 to 3, provided that if m or m' is 1, then Q or Q' may bind to either of the two fused rings, and if m or m' is 2 or 3, then Q or Q' may bind to one or both of the fused rings or may form a ring together with the two fused rings;
  • A represents an optionally branched alkylene group of 2-12 carbon atoms or a cyclic group having conjugated double bonds
  • At least one of Y and Y' comprises X or X' which is an optionally branched alkyl group of 1-16 carbon atoms.
  • the present invention further relates to novel bis(aminocarbonylnaphthol) derivatives represented by the general formula [VIII"], [IX"], or [X"]: ##STR5## wherein, Y represents --(CONH) n --X or --COR; Y' represents --(CONH) n --X' or --COR';
  • X and X' each represent an optionally branched alkyl group of 1-16 carbon atoms, an optionally substituted aromatic group, or an optionally substituted heterocyclic group having conjugated double bonds;
  • n an integer 1 or 2;
  • R and R' each represent a hydroxyl group, an optionally branched alkoxy group of 7-30 carbon atoms, a benzyloxy group, a phenyloxy group, or a phenacyloxy group, provided that if one of R and R' is a hydroxyl group, then it may form an acceptable salt;
  • R 2 and R 2 ' each represent a hydrogen atom, an optionally branched alkyl group of 1-6 carbon atoms, an acyl group of 1-6 carbon atoms, or a phenylalkyl group;
  • Q and Q' each represent an optionally branched alkyl group of 1-6 carbon atoms, an optionally branched alkoxy group of 1-6 carbon atoms, a halogen atom, a nitro group, or a nitroso group;
  • n and m' each represent an integer from 0 to 3, provided that if m or m' is 1, then Q or Q' may bind to either of the two fused rings, and if m or m' is 2 or 3, then Q or Q' may bind to one or both of the fused rings or may form a ring together with the two fused rings;
  • A represents an optionally branched alkylene group of 2-12 carbon atoms or a cyclic group having conjugated double bonds
  • At least one of Y and Y' comprises R or R' which is an optionally branched alkoxy group of 7-30 carbon atoms.
  • the compound of the present invention is characterized in that it is a novel condensed azo compound of which fundamental structure comprises a bisamide compound (e.g., PCT/JP97/03638) derived from a naphthol having carboxyl groups at the 3- and 6-positions by amidating one of the carboxyl groups with an aromatic diamine.
  • fundamental structure comprises a bisamide compound (e.g., PCT/JP97/03638) derived from a naphthol having carboxyl groups at the 3- and 6-positions by amidating one of the carboxyl groups with an aromatic diamine.
  • A is an optionally branched alkylene group of 2-12 carbon atoms or a cyclic group having conjugated double bonds.
  • the alkylene group is preferably straight, and those groups which consist of 2-6 carbon atoms are particularly preferred.
  • Preferred cyclic groups having conjugated double bonds are arylene groups and those groups having fundamental structures represented by the general formula [IV]:
  • Ar and Ar' each represent independently an optionally substituted arylene group or a heterocyclic group having conjugated double bonds
  • M represents a single bond, or a group selected from --CH 2 --, --CH ⁇ C(E)-- (wherein E may represent, for example, hydrogen, a halogen atom, a lower alkyl group, or a cyano group), --O--, --S--, --S--S--, --CO--, --COO--, --SO 2 --, --N(T)-- (wherein T represents an optionally substituted phenyl group or a lower alkyl group), --N ⁇ N--, --CH ⁇ CH-- ⁇ --CH ⁇ CH-- (wherein ⁇ represents an arylene group), and the formula [V]: ##STR6## (wherein G represents --O--, --S--, or --NH--)], or the general formula [VI]: ##STR7## [wherein L represents >N--CH 3 , >C ⁇ O, or >C ⁇ S.]
  • arylene groups for example, phenylene, naphthylene, and anthrylene, which may be optionally substituted;
  • substituents on A may include lower alkyl groups such as methyl, ethyl, isopropyl, propyl, n-butyl, isobutyl, and tert-butyl, lower alkoxy groups such as methoxy and ethoxy, halogens such as fluorine, chlorine, bromine, and iodine, cyano, and nitro.
  • the moiety constituting the group X or X' is, for example, an optionally branched alkyl group of 1-16, and preferably 1-12, carbon atoms, an optionally substituted aromatic group such as phenyl, naphthyl, or anthraquinonyl group, or an optionally substituted heterocyclic group having conjugated double bonds such as benzimidazolonyl, carbazolyl, pyridyl, thiazolyl, benzothiazolyl, imidazolyl, indolyl, thiofuryl phenothiazinyl, acridinyl, or quinolinyl group, provided that in the general formulas [VIII'], [IX'], and [X'], at least one of Y and Y' comprises X or X' which is an optionally branched alkyl group of 1-16 carbon atoms.
  • substitutes on such aromatic or heterocyclic groups may include halogens, nitro, lower alkyl, lower alkoxy, cyano, phenoxy, and amide (e.g., phenylaminocarbonyl) groups, and such phenoxy and amide groups may further have additional substituent(s) such as halogen, lower alkyl, lower alkoxy, alkylaminosulfonyl, and nitrile. Since color and vividness of the compounds can be effectively changed by introducing different kinds of substituent onto these aromatic or heterocyclic groups, a series of azo compounds having different color and/or vividness can be easily obtained.
  • Y and Y' may also represent COR or COR'.
  • R and R' each represent a hydroxyl group, an optionally branched alkoxy group of 1-30, and preferably 1-20, carbon atoms (with the proviso that in the general formulas [VIII'], [IX'], and [X'], they each represent an optionally branched alkoxy group of 1-6, and preferably 1-4, carbon atoms, and in the general formulas [VIII"], [IX"], and [X”], they each represent an optionally branched alkoxy group of 7-30, and preferably 7-20, carbon atoms), a benzyloxy group, a phenoxy group, or a phenacyloxy group, and the aromatic rings contained in such groups may have substituent(s), provided that in the general formulas [VIII"], [IX"], and [X"], at least one of Y and Y' comprise R or R' which represents an optionally branched alkoxy group of 7-30 carbon
  • Y and Y' are --CONH--X and --CONH--X', respectively.
  • the groups R 2 and R 2 ' is each a hydrogen atom, an optionally branched alkyl group of 1-6, and preferably 1-4, carbon atoms, with a methyl or ethyl group being preferred; an acyl group of 1-6, preferably 1-4, carbon atoms, and in particular an acetyl group; or a phenylalkyl group which may optionally have substituent(s) such as a halogen atom or a lower alkyl group of which number of carbon atoms is preferably 1-6.
  • Z and Z' constituting the azo groups are each an optionally substituted monovalent aromatic group.
  • This aromatic group may be a fused ring with heterocyclic group(s). Typical examples of such group are phenyl, naphthyl, anthryl, indenyl, fluorenyl, indolyl, benzothiazolyl, quinolinyl, and carbazolyl groups.
  • substituent are halogens, lower alkyl, in particular methyl, cyano, nitro, alkoxy, amide, sulfo, alkylaminosulfonyl, aminocarbonyl, phenoxy, alkoxycarbonyl, hydroxy, and benzoylamino groups.
  • a particularly preferred aromatic group is a phenyl group.
  • the two naphthalene nuclei each may be substituted with Q or Q' which may each represent, for example, any of a lower alkyl groups (preferably of 1-4 carbon atoms), a lower alkoxy group (preferably of 1-4 carbon atoms), a halogen atom, a nitro group and a nitroso group.
  • Q or Q' may each represent, for example, any of a lower alkyl groups (preferably of 1-4 carbon atoms), a lower alkoxy group (preferably of 1-4 carbon atoms), a halogen atom, a nitro group and a nitroso group.
  • the condensed azo compounds of the present invention may be prepared, for example, according to the reaction scheme described below. Although the following reaction scheme relates to condensed azo compounds [I'] in which the carboxyl groups at the 3-positions have been bisamidated by way of example, the condensed azo compounds of the formulas [II] and [III] may also be prepared in the similar manner. ##STR15##
  • the bisamide compound [VIII'] is reacted with a diazonium compound to yield the condensed azo compound [I'].
  • a diazonium compound to yield the condensed azo compound [I'].
  • 2-hydroxynaphthalene-3,6-dicarboxylic acid [XI] obtained by Kolbe-Schmitt or other reaction
  • the carboxyl group at the 3-position is protected by, for example, esterification.
  • the carboxylic acid at the 6-position is converted into the acid chloride using thionyl chloride or the like, and then reacted with an aromatic amine to yield 6-amide compound [XII].
  • the dicarboxylic acid [XI] may also be directly reacted with amines using, for example, phosphorus trichloride or dicyclohexylcarbodiimide to obtain the amide compound.
  • the amide compound thus obtained is reacted with a diazonium compound to yield 1-azo-6-amide compound [XIII] which is then, following if desired the conversion of the carboxyl group at the 3-position into the acid chloride, reacted with an aromatic diamine (e.g., phenylenediamine) to yield the condensed azo compound [I'].
  • an aromatic diamine e.g., phenylenediamine
  • the above reaction may be conducted with an excess of phenylenediamine to obtain the monoamine compound [XIV].
  • This monoamine compound [XIV] may also be obtained by subjecting the 6-amide compound [XII] to a condensation reaction with an excess of phenylenediamine before the reaction with a diazo compound, and then reacting with a diazonium compound.
  • a phenyl amine having a nitro group may be reacted with the 3-carboxyl group of the 6-amide compound [XII] in the presence of phosphorus trichloride and sulfolane to yield 3-(nitrophenylamide) compound, and the nitro group reduced into an amino group using a conventional method.
  • This product may be then reacted with the 6-amide compound [XII] or corresponding acid chloride to yield a bisamide compound which may be then reacted with a diazonium compound to obtain the condensed azo compound [I'].
  • reaction between a carboxyl group and an amino group of aromatic amine may be achieved by firstly converting the carboxyl group into the acid chloride followed by the reaction with the amine, or by directly reacting the carboxyl group with the aromatic amine in the presence of phosphorus trichloride and sulfolane.
  • Examples of the amine may include optionally substituted aromatic amino compounds such as aniline (X or X' is a phenyl group), ⁇ - or ⁇ -aminonaphthalene (X or X' is a naphthyl group), and aminoanthraquinone (X or X' is an anthraquinonyl group), optionally substituted heterocyclic compounds having conjugated double bonds such as aminobenzimidazolone (X or X' is a benzimidazolonyl group), aminocarbazole (X or X' is an aminocarbazolyl group), aminopyridine (X or X' is a pyridyl group), aminothiazole (X or X' is a thiazolyl group), aminobenzothiazole (X or X' is a benzothiazolyl group), and aminoimidazole (X or X' is an imidazolyl group), as
  • substituent on such compounds are halogens, nitro, lower alkyl, alkoxy, cyano, phenoxy, and amide (e.g., phenylaminocarbonyl) groups, and such phenoxy groups and amide groups may further contain additional substituent(s) such as halogen, lower alkyl, lower alkoxy, alkylaminosulfonyl, or nitrite.
  • An azo compound of the present invention may be obtained by coupling the diazonium compound [VII] or [VII'], obtained by diazotizing an aromatic amine with sodium nitrite or the like, to the above 2-hydroxynaphthalene-3,6-dicarboxylic acid or a derivative thereof (e.g., a carboxamide, carboxyureide, or ester).
  • aromatic amine may include aniline, monoamino-fused polycyclic hydrocarbons such as ⁇ - or ⁇ -naphthylamine, monoaminoanthracene, monoaminoindene, and monoaminofluorenone, monoaminoindole, monoaminobenzothiophene, monoaminoquinoline, and monoaminocarbazole.
  • aromatic amines may have substituent(s) such as halogen, lower alkyl (in particular methyl), cyano, nitro, lower alkoxy, amide, sulfo, alkylaminosulfonyl, aminocarbonyl, phenoxy, alkoxycarbonyl, hydroxy, and benzoylamino groups.
  • aromatic amines are anilines.
  • the process for preparing a diazonium compound from an amine is not specifically restricted.
  • the standard method for diazotizing aromatic primary amines with sodium nitrite may be used.
  • the process in which the diazonium compound is further coupled with the above-described 2-hydroxynaphthalene-3,6-dicarboxylic acid or a derivative thereof (e.g., a carboxamide, carboxyureide, or ester) may also be achieved by a conventional method.
  • the azo compounds of the present invention exhibit excellent water resistance, solvent resistance, chemical resistance, and heat resistance, and may be used in pigments, printing inks, paints, colorating agents for plastics, organic photoconductive materials, and the like.
  • FIG. 1 is the infrared absorption spectrum of the compound obtained in Example 1.
  • FIG. 2 is the infrared absorption spectrum of the compound obtained in Example 38.
  • FIG. 3 is the infrared absorption spectrum of the compound obtained in Example 39.
  • FIG. 4 is the infrared absorption spectrum of the compound obtained in Example 40.
  • FIG. 5 is the infrared absorption spectrum of the compound obtained in Example 41.
  • FIG. 6 is the infrared absorption spectrum of the compound obtained in Example 42.
  • FIG. 7 is the infrared absorption spectrum of the compound obtained in Example 43.
  • FIG. 8 is the infrared absorption spectrum of the compound obtained in Example 44.
  • FIG. 9 is the infrared absorption spectrum of the compound obtained in Example 45.
  • amine component 1.45 g of 2,5-dichloroaniline is suspended in 12.0 g of water, and 2.3 g of 36% hydrochloric acid is added thereto. While maintaining the temperature at 0-5° C., a solution of 0.7 g of sodium nitrite dissolved in 10 g of water is then added dropwise to achieve diazotization. Subsequently, 0.8 g of acetic acid, 0.15 g of Pearlite®, 0.15 g Carboraffin® added, and the mixture is filtered. The temperature is kept at not over 10° C. during this procedure.
  • a coupler component 3.1 g of 1,4-bis(2'-hydroxy-6'-phenylaminocarbonyl-naphth-3'-yl-carbonylamino)phenylene is suspended in 124 g of N-methyl-2-pyrrolidone, a solution of 1.0 g of sodium hydroxide dissolved in 10 g of water added thereto, and kept at 15° C. following dissolution. To this, the clear diazo solution described above is added for 20 to 30 minutes to effect the coupling reaction. After stirring for 60 minutes, the reaction mixture is heated to 70° C., and further stirred for about 30 minutes. The reaction mixture was then gradually cooled, and suction-filtered at room temperature.
  • the infrared absorption spectrum (diffuse reflection) of this product is shown in FIG. 1.
  • Example 1 For the condensed azo compound obtained in Example 1, the properties are shown in Table 1, including water resistance, chemical resistance, solvent resistance, light resistance, and heat resistance.
  • One part of the sample is added to 20 parts of water, and dispersed by sonicating for 20 minutes. After boiling for one minutes, the mixture is cooled, and filtered. The color of the filtrate was then observed, and evaluated according to the criteria A-E described below.
  • One part of the sample is added to 20 parts of 5% aqueous hydrochloric acid or sodium hydroxide, and dispersed by sonicating for 5 minutes. After filtration, the color of the filtrate was observed, and evaluated according to the criteria A-E described below.
  • One part of the sample is added to 20 parts of acetone, methanol, xylene, or ethyl acetate, and dispersed by sonicating 5 minutes. After filtration, the color of the filtrate was observed, and evaluated according to the following criteria A-E.
  • a half of the test piece of 3) is masked, and then irradiated in a feather meter (Shimadzu Corporation; Suntester® XF-180/xenon lamp) for 100 hours.
  • the masked and unmasked areas are each subjected to colorimetry, and the light resistance is evaluated on the basis of the color difference ⁇ E between the two areas.
  • test sheet obtained in 1) is cut into 30 mm x 30 mm pieces.
  • test pieces of 2) are left in an incubator at 170° C. for 60 minutes.
  • the test pieces were subjected to colorimetry before and after the heating, and the heat resistance was evaluated on the basis of the color difference ⁇ E.
  • Example 2 In the same manner as Example 1, except that the amines and couplers indicated in Table 3 were used as the amine and coupler components, respectively, azo compounds were synthesized. The melting/decomposing point for each azo compound synthesized is shown in Table 2.
  • Example 29 In the same manner as Example 29, except that 2-methoxy-5-diethylaminosulfonylaniline was substituted for 4-nitrotoluidine to obtain the corresponding diazonium borofluoride, 1.08 g of dark bluish red powder which contained the intended product as a major component was obtained (melting/decomposing point: 248.4° C. (melt), 301.7° C. (dec.)).
  • Example 26 One part of the azo compound obtained in Example 26 was dispersed with one part of a poly(vinyl butyral) (Sekisui Chemical Co., S-LEC BH-3) and 10 parts of cyclohexanone using ball mill. The dispersed azo compound was applied onto an aluminum plate using bar applicator, and then dried. At this stage, the thickness of the film was about 0.5 ⁇ m.
  • the half-exposure (E 1/2 ) as a sensitivity of photosensitive material was measured for the above photosensitive material using an electrostatic copy paper tester (K. K. Kawaguchi Denki Seisakusho Model EPA-8100).
  • the material was firstly electrified by corona discharge at -5.0 kV in darkness, and then exposed to white light at an illumination of 20 luxes in order to determine the exposure dose required to decay the surface potential to the half of the initial value.
  • E 1/2 The half-exposure (E 1/2 ) thus determined was 6.8 lux ⁇ sec. And the surface potential after sufficient exposure (residual potential) (after exposed to 200 lux ⁇ sec) was -1 V.
  • Example 31 In the same manner as Example 31, except that 2.68 g of 1,4-bis(2'-hydroxy-6'-hydroxynaphth-3'-ylcarbonylamino)phenylene was substituted for 1,6-bis(2'-hydroxy-3'-hydroxynaphth-6'-ylcarbonylamino)hexane used in Example 31, 3.92 g of dark bluish red powder was obtained (melting/decomposing point: 472.8° C. (dec.)).
  • Example 6 In the same manner as Example 1, except that the amines and couplers indicated in Table 7 were used as the amine and coupler components, respectively, azo compounds were synthesized. The melting/decomposing point for each azo compound synthesized is shown in Table 6.
  • An acid chloride is prepared in the usual manner from 7.39 g of 2-hydroxy-6-hydroxycarbonyl-3-methoxycarbonylnaphthalene, and a solution of 6.82 g of n-dodecylamine dissolved in 25 g of N-methyl-2-pyrrolidone and 13 g of xylene is added thereto dropwise at 80° C. After allowing to proceed the reaction for about 18 hours, the reaction is ice-cooled, and the precipitate is recovered by filtration.
  • the precipitate (10.48 g) washed with acetone is dissolved in 100 g of N,N-dimethylformamide at 60° C., and a solution of 3.2 g of sodium carbonate dissolved in 100 g of water and 30 g of methanol is added.
  • the reaction is allowed to proceed for 2 hours at 80° C., and 100 g of water is further added following removal of insoluble matter.
  • the solution is adjusted to pH 2.
  • the precipitate formed is recovered by filtration, washed with warm water and methanol, and dried.
  • the crystal (1.02 g) thus obtained is suspended in 22.16 g of tetrahydrofuran, added 0.35 g of thionyl chloride, and reacted for about 15 hours in ice bath.
  • Example 38 In the same manner as Example 38, except that n-octyl alcohol was substituted for n-dodecylamine used in Example 38, 0.38 g of skin colored powder was obtained (melting/decomposing point: 95.2° C. (melt), 320.8° C. (dec.)).
  • Example 38 In the same manner as Example 38, except that 1-hexadecanol was substituted for n-dodecylamine used in Example 38, 0.61 g of skin colored powder was obtained (melting/decomposing point: 127.5° C. (melt), 329.5° C. (dec.)).
  • the solid thus obtained is suspended in 200 g of methanol, 50 g of 24% sodium hydroxide added, and reacted at 50° C. for 6 hours. To this, 200 g of water is added, pH adjusted to 2, and the precipitate recovered by filtration. The precipitate was washed with warm water and methanol, and then dried to yield 2.6 g of 1,4-bis(2-hydroxy-3-methoxycarbonylnaphth-6-ylcarbonylamino)phenylene.
  • an acid chloride is prepared from the above compound in the usual manner, and a solution of 2.6 g of n-amyl alcohol dissolved in 20 g of N-methyl-2-pyrrolidone is added thereto. After allowing to proceed the reaction at 80° C. for 18 hours, 50 g of methanol is added, and the precipitate is recovered by filtration. The precipitate was washed thoroughly with methanol, and dried to yield 0.68 g of off-white powder (melting/decomposing point: 300.4° C. (dec.)).
  • Example 41 In the same manner as Example 41, except that 7.3 g of 2-hexyldecanol was substituted for n-amyl alcohol used in Example 41, 0.83 g of off-white powder was obtained (melting/decomposing point: 225.8° C. (melt)).
  • Example 41 In the same manner as Example 41, except that 3.2 g of benzyl alcohol was substituted for n-amyl alcohol used in Example 41, 0.76 g of off-white powder was obtained (melting/decomposing point: 283.0° C. (melt)).
  • an acid chloride is prepared from the above compound in the usual manner, and a solution of 1.00 g of 2-hydroxy-6-(4'-aminophenylaminocarbonyl)-3-phenylaminocarbonylnaphthalene dissolved in 60.0 g of N-methyl-2-pyrrolidone is added thereto. After allowing to proceed the reaction at 80° C. for 18 hours, 200 g of methanol is added, and the precipitate is recovered by filtration. The precipitate was washed thoroughly with methanol, and dried to yield 0.99 g of off-white powder (melting/decomposing point: 296.8° C. (dec.)).
  • Example 44 In the same manner as Example 44, except that 1.00 g of 2-hydroxy-6-(3'-aminophenylaminocarbonyl)-3-phenylaminocarbonylnaphthalene was substituted for 2-hydroxy-6-(4'-aminophenylcarbonyl)-3-phenylaminocarbonylnaphthalene used in Example 44, 0.93 g of tan powder was obtained (melting/decomposing point: 311.2° C. (dec.)).

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US20050186495A1 (en) * 2004-02-20 2005-08-25 Norman Herron Charge transport compounds and electronic devices made with such compounds
US7083674B1 (en) * 2005-09-06 2006-08-01 Toyo Ink Mfg. Co., Ltd. Pigment dispersant, and pigment composition, pigment dispersion and printing ink using the same
US20060241227A1 (en) * 2005-04-19 2006-10-26 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Pigment dispersants and their use
US20070251414A1 (en) * 2003-11-28 2007-11-01 Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo Red Ink Composition for Color Filter
US20090005546A1 (en) * 2007-06-29 2009-01-01 Ricoh Company, Ltd. Azo compound and method of preparing the azo compound
US7476260B2 (en) 2004-04-08 2009-01-13 Ciba Specialty Chemicals Corp. Disulfide dyes, composition comprising them and method of dyeing hair
US20130000511A1 (en) * 2010-01-15 2013-01-03 Fujifilm Corporation Pigment composition, ink for inkjet recording, coloring composition for color filter, and color filter
US8617720B2 (en) 2009-12-21 2013-12-31 E I Du Pont De Nemours And Company Electroactive composition and electronic device made with the composition

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JP6179121B2 (ja) * 2013-02-20 2017-08-16 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色剤、着色組成物、およびカラーフィルタ
JP6172488B1 (ja) * 2017-02-28 2017-08-02 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色剤、着色組成物、およびカラーフィルタ
JP6368844B1 (ja) * 2017-08-25 2018-08-01 東洋インキＳｃホールディングス株式会社 アゾ顔料、カラーフィルタ用着色剤、着組成物およびカラーフィルタ

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US20070251414A1 (en) * 2003-11-28 2007-11-01 Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo Red Ink Composition for Color Filter
US7011871B2 (en) 2004-02-20 2006-03-14 E. I. Du Pont De Nemours And Company Charge transport compounds and electronic devices made with such compounds
US20050186495A1 (en) * 2004-02-20 2005-08-25 Norman Herron Charge transport compounds and electronic devices made with such compounds
US7476260B2 (en) 2004-04-08 2009-01-13 Ciba Specialty Chemicals Corp. Disulfide dyes, composition comprising them and method of dyeing hair
US20060241227A1 (en) * 2005-04-19 2006-10-26 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Pigment dispersants and their use
US7347894B2 (en) * 2005-04-19 2008-03-25 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Pigment dispersants and their use
US7083674B1 (en) * 2005-09-06 2006-08-01 Toyo Ink Mfg. Co., Ltd. Pigment dispersant, and pigment composition, pigment dispersion and printing ink using the same
US20090005546A1 (en) * 2007-06-29 2009-01-01 Ricoh Company, Ltd. Azo compound and method of preparing the azo compound
US8232376B2 (en) 2007-06-29 2012-07-31 Ricoh Company, Ltd. Azo compound and method of preparing the azo compound
US8541557B2 (en) 2007-06-29 2013-09-24 Ricoh Company, Ltd. Azo compound and method of preparing the azo compound
US8617720B2 (en) 2009-12-21 2013-12-31 E I Du Pont De Nemours And Company Electroactive composition and electronic device made with the composition
US20130000511A1 (en) * 2010-01-15 2013-01-03 Fujifilm Corporation Pigment composition, ink for inkjet recording, coloring composition for color filter, and color filter
US8828132B2 (en) * 2010-01-15 2014-09-09 Fujifilm Corporation Pigment composition, ink for inkjet recording, coloring composition for color filter, and color filter

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WO1998041580A1 (fr) 1998-09-24
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